Bedroom – King Bed
Bedroom – King Bed
Open Living Area
Open Living & Kitchen Area
Living Room – Sofa Bed

Luxury 1BR: Sleek Kitchen + City Charm | Suite 2

1 bedroom·1 bath
Boston • Massachusetts
$250 – $1,107/ night(excl. fees & taxes)
Cozy King Bedroom
Cozy King Bedroom
Enjoy the view from the large bay windows in the sitting area
Relaxing Den Area with Pull Out Seating
Relaxing Den Area – TV & Pull Out Seating

Elegant 1BR Plus: Cityscape Views + King and pull out Queen| Suite 5

2 bedrooms·1 bath
Boston • Massachusetts
$283 – $1,769/ night(excl. fees & taxes)
Cozy King Bedroom
Fantastic City View Seating from the large bay windows
Cozy King Bedroom with City View
Relaxing Den Area with Pull Out Seating
Relaxing Den Area – TV & Pull Out Seating

Cityscape 1BR Plus: King + Queen Pull-out | Suite 7

2 bedrooms·1 bath
Boston • Massachusetts
$283 – $1,277/ night(excl. fees & taxes)
Bedroom 1 – King Bed
Bedroom – King Bed & TV
Bedroom – King Bed
Bedroom 2 – Queen Bed
Bedroom – Queen Bed

Trendy 2BR Plus Family Getaway | Suite 4

2 bedrooms·1 bath
Boston • Massachusetts
$351 – $1,482/ night(excl. fees & taxes)
City View Bedroom – King Bed
Fantastic City View Seating
Bedroom – King Bed
Living Area – TV & Seating
Open Living Area

Front Row City Views: 1BR Suite with King Bed | Suite 3

1 bedroom·1 bath
Boston • Massachusetts
$250 – $1,249/ night(excl. fees & taxes)
King size master bed with privacy curtains
King size bed with all comforts
Lofty open space
Open space layout keeps everyone together weather in the kitchen or livingroom
Livingroom featuring a large TV

The Urban Hideout Loft: Sleeps 4 | Private Entrance

0 bedrooms·1 bath
Boston • Massachusetts
$250 – $1,202/ night(excl. fees & taxes)
living and dining area
Back of house
Front entry
livingroom
First floor full bathroom

Boston Historical Urban Oasis

7 bedrooms·3 baths
Boston • Massachusetts

$2,498.11 USD total for 3 nights

Sep 7 – 10, 2026

Eating area and sleeping area
Kitchen After 2025 Renovation showing clothes washer-dryer
Back yard from back deck
Frog on deck
House From Street

Cambridge Studio Apartment

1 bedroom·1 bath
Cambridge • Massachusetts
4.67(400 reviews)

$450.00 USD total for 3 nights

Sep 7 – 10, 2026

Living room
Bedroom #1
Bedroom #1 Queen bed
Bedroom #2
Bedroom #2 with queen bed and crib

Boston's Jamaica Plain w/ parking, A/C, laundry

2 bedrooms·1 bath
Boston • Massachusetts
4.81(120 reviews)

$1,069.06 USD total for 3 nights

Sep 7 – 10, 2026

Bright, Spacious Bedroom
Bright and spacious room, comfy bed.
Entry Hallway
Private Bath
Cape Ann sunset (up the road at Plum Cove)

Quirky, Bright, Spacious Private Room Near Water

1 bedroom·1 bath
Gloucester • Massachusetts
5(15 reviews)
$159 – $209/ night(excl. fees & taxes)
our place from the beach
full bath
twin beds, back left
Beach Bridge
House front from yard

Beach Bridge

3 bedrooms·1 bath
Gloucester • Massachusetts

$4,235.00 USD total for 7 nights

Sep 7 – 14, 2026

Lakeview Getaway with Hot Tub
Lakeview Getaway with Hot Tub
Lakeview Getaway with Hot Tub
Lakeview Getaway with Hot Tub
Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub

3 bedrooms·2 baths
Billerica • Massachusetts

$1,586.77 USD total for 3 nights

Sep 7 – 10, 2026

Lake Access 4 Bed 3 Bath HOT TUB
HOT TUB TIME!!!
Lake Access 4 Bed 3 Bath HOT TUB
Lake Access 4 Bed 3 Bath HOT TUB
Lake Access 4 Bed 3 Bath HOT TUB

Lake Access 4 Bed 3 Bath HOT TUB

4 bedrooms·3 baths
Billerica • Massachusetts

$1,822.88 USD total for 3 nights

Sep 8 – 11, 2026

Anchor's Away @ The Sail Loft!
living room
Living room with dining table
Comfortable chair
View out windows to White Wharf

"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven

2 bedrooms·1 bath
Rockport • Massachusetts
4.87(143 reviews)

$1,160.10 USD total for 3 nights

Sep 7 – 10, 2026

Living room
The Waterline
The Waterline
The Waterline
Bedroom 1 -Queen Bed

The Waterline

2 bedrooms·1 bath
Rockport • Massachusetts

$1,143.95 USD total for 3 nights

Oct 31 – Nov 3, 2026

Free cancellation
Living Room: Bright space with nautical charm, leather couch, and dining for four! Perfect for relaxing!
Living Room: Relax in style with plush seating, vintage decor, and warm natural light!
Views of Bearskin neck and peeks of the Harbor from windows
Living Room: Sunlight dances through windows, inviting relaxation in stylish comfort and charm!
Bedroom 1 -Queen Bed

The Waterline

2 bedrooms·1 bath
Rockport • Massachusetts
5(17 reviews)

$892.98 USD total for 3 nights

Sep 7 – 10, 2026

The Orca Suite
Sunny 1st floor unit with views
Smart TV in living room for streaming
Leather arm chairs
Living room

The Orca

2 bedrooms·1 bath
Rockport • Massachusetts

$1,000.58 USD total for 3 nights

Nov 3 – 6, 2026

Free cancellation
The Orca Suite
Sunny 1st floor unit with views
Smart TV in living room for streaming
Leather arm chairs
Living room

The Orca

2 bedrooms·1 bath
Rockport • Massachusetts
5(9 reviews)

$975.58 USD total for 3 nights

Oct 17 – 20, 2026

Free cancellation
Living room with Plenty of Sunlight
Living room
Smart TV
Bedroom 1 with Queen bed
Open Beam Ceilings- Sail Hooks still in Posts for mending sails!

The Captain's Quarters

2 bedrooms·1 bath
Rockport • Massachusetts
4.82(150 reviews)
$151 – $329/ night(excl. fees & taxes)
Living Room: Timber beams and natural light create a vibrant space for relaxation and fun!
Living Room: Bright and airy space with unique decor, perfect for relaxation and coastal views!
Living Room: Timber beams and a blend of vintage charm invite relaxation and great conversations!
Bedroom: Charming retreat illuminated by natural light with rustic beams and delightful decor!
Bar style eating counter overlooking Bearskin beck

The Captain's Quarters

2 bedrooms·1 bath
Rockport • Massachusetts
5(10 reviews)

$822.36 USD total for 3 nights

Sep 7 – 10, 2026

The Crow's Nest
The Crow's Nest
The Crow's Nest
The Crow's Nest
The Crow's Nest

The Crow's Nest

1 bedroom·1 bath
Rockport • Massachusetts
$285/ night(excl. fees & taxes)
Charming Loft Kitchen: Enjoy culinary adventures in a sunlit space with rustic beams and modern flair!
The Crow's Nest
The Crow's Nest
The Crow's Nest
The Crow's Nest

The Crow's Nest

1 bedroom·1 bath
Rockport • Massachusetts
5(5 reviews)

$793.61 USD total for 3 nights

Sep 9 – 12, 2026

Oceanside | Family Friendly Oceanfront Home
Oceanside | Family Friendly Oceanfront Home
Oceanside | Family Friendly Oceanfront Home
Oceanside | Family Friendly Oceanfront Home
Oceanside | Family Friendly Oceanfront Home

Oceanside | Family Friendly Oceanfront Home

4 bedrooms·2 baths
Scituate • Massachusetts
5(104 reviews)

$2,085.00 USD total for 4 nights

Sep 20 – 24, 2026

Cedar Point/lighthouse/Oceanview (ocean across st) image 1
Cedar Point/lighthouse/Oceanview (ocean across st) image 2
Cedar Point/lighthouse/Oceanview (ocean across st) image 3
Cedar Point/lighthouse/Oceanview (ocean across st) image 4
Cedar Point/lighthouse/Oceanview (ocean across st) image 5

Cedar Point/lighthouse/Oceanview (ocean across st)

3 bedrooms·1 bath
Scituate • Massachusetts
5(2 reviews)
$499/ night(excl. fees & taxes)